Sulfenylation of ortho esters. A novel preparation of 2-[(trihalomethyl) thio] alkanoic acids

WL Mendelson, JH Liu, LB Killmer Jr…

Index: Mendelson, Wilford L.; Liu, Jih-Hua; Killmer, Lewis B.; Levinson, Sidney H. Journal of Organic Chemistry, 1983 , vol. 48, # 3 p. 298 - 302

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Citation Number: 18

Abstract

CCI, SCH, COOR CCI, SCH, COOH lla, R= CH, 1 2 b, R= C, H, rapid. When a stream of trifluoromethanesulfenyl chloride14 (bp-4 to 2" C) was bubbled into an ether (or methyl acetate) solution containing an excess of 3a or 3b at-5" C, the yellow color, indicative of the presence of the sulfenyl chloride, was discharged within seconds. 15 Vacuum distillation of the crude reaction product gave the colorless ortho esters 4a or 4b in 75-80% yield. These ...

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